WO2003074476A1 - Novel arylamidine derivative or salt thereof - Google Patents

Novel arylamidine derivative or salt thereof Download PDF

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Publication number
WO2003074476A1
WO2003074476A1 PCT/JP2003/002506 JP0302506W WO03074476A1 WO 2003074476 A1 WO2003074476 A1 WO 2003074476A1 JP 0302506 W JP0302506 W JP 0302506W WO 03074476 A1 WO03074476 A1 WO 03074476A1
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WO
WIPO (PCT)
Prior art keywords
salt
derivative
substituted
arylamidine derivative
optionally substituted
Prior art date
Application number
PCT/JP2003/002506
Other languages
French (fr)
Japanese (ja)
Inventor
Kazuya Hayashi
Katsuji Ojima
Kozo Hori
Hiroyuki Okujo
Junichi Mitsuyama
Kazuto Kunitani
Keisuke Tohdo
Original Assignee
Toyama Chemical Co., Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to MXPA04008526A priority Critical patent/MXPA04008526A/en
Priority to US10/506,422 priority patent/US7291617B2/en
Priority to EP03743600A priority patent/EP1481966B1/en
Priority to IL16379803A priority patent/IL163798A0/en
Priority to NZ534962A priority patent/NZ534962A/en
Priority to SI200332046T priority patent/SI1481966T1/en
Priority to JP2003572948A priority patent/JP4320260B2/en
Priority to CA2477212A priority patent/CA2477212C/en
Application filed by Toyama Chemical Co., Ltd. filed Critical Toyama Chemical Co., Ltd.
Priority to KR1020047013953A priority patent/KR100915979B1/en
Priority to AT03743600T priority patent/ATE517080T1/en
Priority to DK03743600.3T priority patent/DK1481966T3/en
Priority to AU2003211692A priority patent/AU2003211692B2/en
Priority to BRPI0308207A priority patent/BRPI0308207B8/en
Publication of WO2003074476A1 publication Critical patent/WO2003074476A1/en
Priority to ZA2004/06717A priority patent/ZA200406717B/en
Priority to IL163798A priority patent/IL163798A/en
Priority to NO20043914A priority patent/NO333800B1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/10—Antimycotics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
    • C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
    • C07C257/18—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
    • C07C259/12—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines
    • C07C259/18—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines having carbon atoms of hydroxamidine groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/62—Compounds containing any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylcarbamates
    • C07C271/64—Y being a hydrogen or a carbon atom, e.g. benzoylcarbamates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/14—Nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
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    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
    • C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
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    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/56—Nitrogen atoms
    • C07D211/58—Nitrogen atoms attached in position 4
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    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
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    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
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    • C07D241/08—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
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    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
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    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
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  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Communicable Diseases (AREA)
  • Animal Behavior & Ethology (AREA)
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  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Hydrogenated Pyridines (AREA)
  • Saccharide Compounds (AREA)

Abstract

An arylamidine derivative represented by the general formula (1) (wherein X means optionally substituted lower alkylene or alkenylene; G1 means oxygen, sulfur, or imino; G2 means carbon or nitrogen; Ra means at least one member selected among hydrogen, halogeno, and optionally substituted alkyl, cycloalkyl, and alkoxy; R1 means optionally protected or substituted amidino; and R2 means substituted amino, substituted cyclic amino, etc.) or a salt of the derivative. The derivative or salt has excellent antifungal activity and is highly safe. It is hence useful as a fungicide with satisfactory behavior in the body.
PCT/JP2003/002506 2002-03-06 2003-03-04 Novel arylamidine derivative or salt thereof WO2003074476A1 (en)

Priority Applications (16)

Application Number Priority Date Filing Date Title
KR1020047013953A KR100915979B1 (en) 2002-03-06 2003-03-04 Novel arylamidine derivative or salt thereof
US10/506,422 US7291617B2 (en) 2002-03-06 2003-03-04 Arylamidine derivative or salt thereof
AT03743600T ATE517080T1 (en) 2002-03-06 2003-03-04 NEW ARYLAMIDINE DERIVATIVE OR SALT FROM IT
NZ534962A NZ534962A (en) 2002-03-06 2003-03-04 Novel arylamidine derivative or salt thereof
SI200332046T SI1481966T1 (en) 2002-03-06 2003-03-04 Novel arylamidine derivative or salt thereof
JP2003572948A JP4320260B2 (en) 2002-03-06 2003-03-04 Novel arylamidine derivatives or salts thereof
CA2477212A CA2477212C (en) 2002-03-06 2003-03-04 Novel arylamidine derivative or salt thereof
MXPA04008526A MXPA04008526A (en) 2002-03-06 2003-03-04 Novel arylamidine derivative or salt thereof.
EP03743600A EP1481966B1 (en) 2002-03-06 2003-03-04 Novel arylamidine derivative or salt thereof
IL16379803A IL163798A0 (en) 2002-03-06 2003-03-04 Novel arylamidine derivative or salt thereof
DK03743600.3T DK1481966T3 (en) 2002-03-06 2003-03-04 New arylamidine derivative or salt thereof
AU2003211692A AU2003211692B2 (en) 2002-03-06 2003-03-04 Novel arylamidine derivative or salt thereof
BRPI0308207A BRPI0308207B8 (en) 2002-03-06 2003-03-04 arylamidine derivative or a salt thereof, compound, and, antifungal agent
ZA2004/06717A ZA200406717B (en) 2002-03-06 2004-08-24 Novel arylamidine derivative or salt thereof
IL163798A IL163798A (en) 2002-03-06 2004-08-30 Arylamidine derivative or salt thereof and antifungal agent comprising it
NO20043914A NO333800B1 (en) 2002-03-06 2004-09-20 Arylamidine derivative or salt thereof and antifungal agent containing the same

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2002/60618 2002-03-06
JP2002060618 2002-03-06

Publications (1)

Publication Number Publication Date
WO2003074476A1 true WO2003074476A1 (en) 2003-09-12

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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005097298A (en) * 2003-09-05 2005-04-14 Toyama Chem Co Ltd New arylamidine derivative or its salt
WO2006003881A1 (en) * 2004-06-30 2006-01-12 Toyama Chemical Co., Ltd. Novel arylamidine derivative, salt thereof, and antifungal containing these
WO2006011499A1 (en) * 2004-07-28 2006-02-02 Toyama Chemical Co., Ltd. Novel arylamidine derivative, salt thereof, and antifungal containing these
WO2006021833A2 (en) * 2003-11-25 2006-03-02 University Of Cincinnati Bisbenzamidines for the treatment of pneumonia
WO2006109642A1 (en) * 2005-04-07 2006-10-19 Toyama Chemical Co., Ltd. Pharmaceutical composition and method using antifungal agent in combination
WO2007055197A1 (en) * 2005-11-09 2007-05-18 Toyama Chemical Co., Ltd. Method for producing 4-(3-(4-(3-(4-cyanophenoxy)propyl)- 1-piperidinyl)propoxy)benzonitrile and intermediate thereof
WO2007074868A1 (en) * 2005-12-29 2007-07-05 Toyama Chemical Co., Ltd. Novel arylamidine derivative, salt thereof and antifungal agent containing those
WO2008029810A1 (en) * 2006-09-07 2008-03-13 Ishihara Sangyo Kaisha, Ltd. Phenylguanidine derivative or salt thereof, and pest control agent containing them as active ingredient
WO2012043701A1 (en) * 2010-09-30 2012-04-05 富山化学工業株式会社 Transdermal absorption preparation
WO2013062024A1 (en) * 2011-10-28 2013-05-02 石原産業株式会社 Plant disease control agent containing arylamidine derivative or salt thereof
WO2015087857A1 (en) * 2013-12-10 2015-06-18 日本曹達株式会社 Aryl amidine compound and bactericidal agent
WO2016047550A1 (en) * 2014-09-24 2016-03-31 日本曹達株式会社 Agricultural and horticultural fungicide containing aryl amidine compound
JP2016222655A (en) * 2015-06-03 2016-12-28 日本曹達株式会社 Amidine compound and bactericidal agent
US10111437B2 (en) 2015-06-03 2018-10-30 Nippon Soda Co., Ltd. Substituted guanidines as fungicides

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US8912359B2 (en) * 2003-11-25 2014-12-16 University Of Cincinnati Bisbenzamidines for the treatment of pneumonia
PT2070536E (en) * 2006-10-06 2012-03-06 Toyama Chemical Co Ltd Pharmaceutical composition comprising phenylamidine derivative and method of using the pharmaceutical composition in combination with antifungal agent
TWI395735B (en) * 2007-07-04 2013-05-11 Toyama Chemical Co Ltd Novel crystals of 4-{3-[4-(3-{4-[amino(butoxycarbonylimino) methyl]phenoxy}propyl)-1-piperidinyl]propoxy}-n'-(butoxycarbonyl) benzamidine
EP2606726A1 (en) * 2011-12-21 2013-06-26 Bayer CropScience AG N-Arylamidine-substituted trifluoroethylsulfide derivatives as acaricides and insecticides

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB868552A (en) 1957-12-03 1961-05-17 Wellcome Found Improvements in or relating to novel amidines and the preparation thereof
EP0805149A1 (en) 1994-12-01 1997-11-05 Toyama Chemical Co., Ltd. Novel 2,3-diketopiperazine derivative or salt thereof
EP1178038A1 (en) 2000-08-04 2002-02-06 Aventis Cropscience S.A. Fungicidal phenylamidine derivatives

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB868552A (en) 1957-12-03 1961-05-17 Wellcome Found Improvements in or relating to novel amidines and the preparation thereof
EP0805149A1 (en) 1994-12-01 1997-11-05 Toyama Chemical Co., Ltd. Novel 2,3-diketopiperazine derivative or salt thereof
EP1178038A1 (en) 2000-08-04 2002-02-06 Aventis Cropscience S.A. Fungicidal phenylamidine derivatives

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
BIOORGANIC AND MEDICINAL CHEMISTRY LETTERS, vol. 7, 1997, pages 521 - 526
JOURNAL OF MEDICINAL CHEMISTRY, vol. 33, 1990, pages 1252 - 1257
TIDWELL R.R. ET AL.: "Analogs of 1,5-bis(4-amidinophenoxy) pentane (pentamidine) in the treatment of experimental pneumocystis carinii pneumonia", JOURNAL OF MEDICINAL CHEMISTRY, vol. 33, no. 4, 1990, pages 1252 - 1257, XP000644781 *

Cited By (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005097298A (en) * 2003-09-05 2005-04-14 Toyama Chem Co Ltd New arylamidine derivative or its salt
WO2006021833A2 (en) * 2003-11-25 2006-03-02 University Of Cincinnati Bisbenzamidines for the treatment of pneumonia
WO2006021833A3 (en) * 2003-11-25 2006-07-13 Univ Cincinnati Bisbenzamidines for the treatment of pneumonia
NO339158B1 (en) * 2004-06-30 2016-11-14 Toyama Chemical Co Ltd Salt of arylamidine derivative and anti-fungal agent containing this
WO2006003881A1 (en) * 2004-06-30 2006-01-12 Toyama Chemical Co., Ltd. Novel arylamidine derivative, salt thereof, and antifungal containing these
KR101169694B1 (en) * 2004-06-30 2012-07-31 토야마 케미칼 컴퍼니 리미티드 Novel arylamidine derivative, salt thereof, and antifungal containing these
JP4885722B2 (en) * 2004-06-30 2012-02-29 富山化学工業株式会社 Novel arylamidine derivatives and salts thereof, and antifungal agents containing them
CN100567267C (en) * 2004-06-30 2009-12-09 富山化学工业株式会社 Arylamidine derivative, its salt and contain these anti-mycotic agent
US7700623B2 (en) 2004-06-30 2010-04-20 Toyama Chemical Co., Ltd. Arylamidine derivative, salt thereof, and antifungal containing these
AU2005258613B2 (en) * 2004-06-30 2011-03-17 Toyama Chemical Co., Ltd. Novel arylamidine derivative, salt thereof, and antifungal containing these
JP5021308B2 (en) * 2004-07-28 2012-09-05 富山化学工業株式会社 Novel arylamidine derivatives and salts thereof, and antifungal agents containing them
WO2006011499A1 (en) * 2004-07-28 2006-02-02 Toyama Chemical Co., Ltd. Novel arylamidine derivative, salt thereof, and antifungal containing these
JPWO2006011499A1 (en) * 2004-07-28 2008-05-01 富山化学工業株式会社 Novel arylamidine derivatives and salts thereof, and antifungal agents containing them
NO339713B1 (en) * 2005-04-07 2017-01-23 Toyama Chemical Co Ltd Arylamidine derivatives and pharmaceutical compositions containing the same for use in fungicides in combination
CN101151032B (en) * 2005-04-07 2011-06-22 富山化学工业株式会社 Pharmaceutical composition and method using antifungal agent in combination
JP5216323B2 (en) * 2005-04-07 2013-06-19 富山化学工業株式会社 Pharmaceutical composition and method of using antifungal agent in combination
WO2006109642A1 (en) * 2005-04-07 2006-10-19 Toyama Chemical Co., Ltd. Pharmaceutical composition and method using antifungal agent in combination
JP5314284B2 (en) * 2005-11-09 2013-10-16 富山化学工業株式会社 Process for producing 4- (3- (4- (3- (4-cyanophenoxy) propyl) -1-piperidinyl) propoxy) benzonitrile and intermediates thereof
WO2007055197A1 (en) * 2005-11-09 2007-05-18 Toyama Chemical Co., Ltd. Method for producing 4-(3-(4-(3-(4-cyanophenoxy)propyl)- 1-piperidinyl)propoxy)benzonitrile and intermediate thereof
AU2006330408B2 (en) * 2005-12-29 2011-10-13 Toyama Chemical Co., Ltd. Novel arylamidine derivative, salt thereof and antifungal agent containing those
US8536343B2 (en) 2005-12-29 2013-09-17 Toyama Chemical Co., Ltd. Arylamidine derivative, salt thereof and antifungal agent containing those
KR101359363B1 (en) 2005-12-29 2014-02-07 토야마 케미칼 컴퍼니 리미티드 Novel arylamidine derivative, salt thereof and antifungal agent containing those
WO2007074868A1 (en) * 2005-12-29 2007-07-05 Toyama Chemical Co., Ltd. Novel arylamidine derivative, salt thereof and antifungal agent containing those
WO2008029810A1 (en) * 2006-09-07 2008-03-13 Ishihara Sangyo Kaisha, Ltd. Phenylguanidine derivative or salt thereof, and pest control agent containing them as active ingredient
WO2012043701A1 (en) * 2010-09-30 2012-04-05 富山化学工業株式会社 Transdermal absorption preparation
WO2013062024A1 (en) * 2011-10-28 2013-05-02 石原産業株式会社 Plant disease control agent containing arylamidine derivative or salt thereof
WO2015087857A1 (en) * 2013-12-10 2015-06-18 日本曹達株式会社 Aryl amidine compound and bactericidal agent
JPWO2015087857A1 (en) * 2013-12-10 2017-03-16 日本曹達株式会社 Aryl amidine compounds and fungicides
WO2016047550A1 (en) * 2014-09-24 2016-03-31 日本曹達株式会社 Agricultural and horticultural fungicide containing aryl amidine compound
JP2016222655A (en) * 2015-06-03 2016-12-28 日本曹達株式会社 Amidine compound and bactericidal agent
US10111437B2 (en) 2015-06-03 2018-10-30 Nippon Soda Co., Ltd. Substituted guanidines as fungicides

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AU2003211692A1 (en) 2003-09-16
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SI1481966T1 (en) 2011-11-30
BRPI0308207B1 (en) 2017-05-09
CN1642906A (en) 2005-07-20
EP1481966A1 (en) 2004-12-01
IL163798A (en) 2011-04-28
CA2477212C (en) 2011-11-15
KR100915979B1 (en) 2009-09-10
CA2477212A1 (en) 2003-09-12
RU2004129725A (en) 2005-05-10
ES2367359T3 (en) 2011-11-02
AU2003211692B2 (en) 2009-01-15
PL372536A1 (en) 2005-07-25
EP1481966A4 (en) 2005-11-23
NZ534962A (en) 2005-07-29
BR0308207A (en) 2004-12-21
JPWO2003074476A1 (en) 2005-06-30
IL163798A0 (en) 2005-12-18
US20050113424A1 (en) 2005-05-26
KR20040091111A (en) 2004-10-27
MXPA04008526A (en) 2005-07-13
DK1481966T3 (en) 2011-10-24
CY1111780T1 (en) 2015-10-07
US7291617B2 (en) 2007-11-06
PT1481966E (en) 2011-10-19
ATE517080T1 (en) 2011-08-15
NO20043914L (en) 2004-09-20
PL209135B1 (en) 2011-07-29
ZA200406717B (en) 2005-10-26

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